Westside Vacations from $448

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Your Westside Vacation

A great way to experience this city is with a customized Westside vacation package. Stay in the neighborhood of Murray Hill, which is great for distilleries and craft breweries, bars and pubs and dining or go someplace else — our package deals are all about you. Jacksonville Equestrian Center, Crystal Springs Park and Bent Creek Golf Course are just a few of the many sights you'll want to check out during your trip to Westside. Browse Expedia's wide range of travel options and start planning your ultimate vacation to Westside now.

The Latest Westside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Tricove Inn & Suites

Tricove Inn & Suites

2.5 out of 5
Southside
Save 100% on your flight
Price was $706, price is now $448 per person
$448
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
7.2/10 Good! (1,002 reviews)
Away from most noise. Like the business area.

Reviewed on Aug 11, 2025

Hampton Inn Jacksonville Beach/Oceanfront

Hampton Inn Jacksonville Beach/Oceanfront

3 out of 5
Save 100% on your flight
Price was $1,018, price is now $666 per person
$666
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
9.2/10 Wonderful! (2,455 reviews)
Did not have an ocean view, but great friendly service

Reviewed on Oct 8, 2025

Delta Hotels by Marriott Jacksonville Deerwood

Delta Hotels by Marriott Jacksonville Deerwood

4 out of 5
Southside
Save 100% on your flight
Price was $680, price is now $448 per person
$448
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
8.6/10 Excellent! (387 reviews)
Super comfy bed and quiet spot

Reviewed on Oct 7, 2025

DoubleTree by Hilton Hotel Jacksonville Riverfront

DoubleTree by Hilton Hotel Jacksonville Riverfront

4 out of 5
Downtown Jacksonville
Save 100% on your flight
Price was $913, price is now $607 per person
$607
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
6.6/10 (1,383 reviews)
Checking was a breeze staff friendly and hotel was great place when going to see a football game , took the water taxi right in back of hotel . Great walking .

Reviewed on Oct 7, 2025

Hammock Beach Golf Resort & Spa

Hammock Beach Golf Resort & Spa

4 out of 5
Save 100% on your flight
Price was $946, price is now $643 per person
$643
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Daytona Beach (DAB)
8.6/10 Excellent! (1,009 reviews)
The patio door was not able to be opened without the assistance of the engineer. The freezer had no ice— it had been turned off. The tvs did not work the first night—the picture and the sound were broken up and garbled. The second night we needed the help of the engineer again as all three tvs said “no signal”. The showers were difficult to operate without first knowing how they worked. The twin bed’s mattress was very uncomfortable. All of the outlets in the kitchen had been shut off, but we did figure out to turn them on. The room itself was lovely, really enjoyed the ocean view and we loved the pools, the beach and the restaurants! Every staff person was wonderful.

Reviewed on Sep 27, 2025

Where to stay in Westside

Find the best Westside areas and neighborhoods for the activities you enjoy most. Learn more about Westside
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Southside

3 out of top 10 points of interest in this area
4/5(912 area reviews)

If you're spending some time in Southside, St. Johns Town Center and The Avenues are top sights worth seeing.

Find hotels in Southside

Westside Hotel Deals

Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station

Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station

2.5 out of 5
8001 PARRAMORE ROAD, Jacksonville, FL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $134 total per night from Oct 12 to Oct 13
$134 total
Oct 12 - Oct 13
Total with taxes and fees
9.4/10 Exceptional! (1,001 reviews)
"This hotel was superb. Very clean and fresh smelling. Even the stairwell was clean and had the scent of Febreze. The staff was amazing! The breakfast options were great."

Reviewed on Oct 3, 2025

Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station
Margaritaville Jacksonville Beach

Margaritaville Jacksonville Beach

2.5 out of 5
715 1st St N, Jacksonville Beach, FL
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $197 total per night from Oct 9 to Oct 10
$197 total
Oct 9 - Oct 10
Total with taxes and fees
8.8/10 Excellent! (3,240 reviews)
"Nice beach view!"

Reviewed on Oct 4, 2025

Margaritaville Jacksonville Beach
Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
225 E Coastline Dr, Jacksonville, FL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $186 total per night from Oct 17 to Oct 18
$186 total
Oct 17 - Oct 18
Total with taxes and fees
8.8/10 Excellent! (1,300 reviews)
"Staff was very friendly and helpful. The room was spacious and very comfortable. There were a few restaurant options at the hotel all of which were great!"

Reviewed on Sep 27, 2025

Hyatt Regency Jacksonville
See all 2,934 properties in Westside
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Westside

Jacksonville Naval Air Station

Jacksonville Naval Air Station

4/5(300 reviews)

After visiting Jacksonville Naval Air Station, make a plan to see the other sights and activities in Jacksonville. Experience the lively festivals or attend a sporting event in this family-friendly area.

Jacksonville Naval Air Station

Florida Yacht Club Marina

Explore the waterfront in Jacksonville with a trip to Florida Yacht Club Marina. Amble around this family-friendly area's riverfront or experience its acclaimed theater scene.

Florida Yacht Club Marina

Ortega Yacht Club Marina

Explore the waterfront in Jacksonville with a trip to Ortega Yacht Club Marina. Amble around the area's riverfront or attend a sporting event.

Ortega Yacht Club Marina

Things to do

Chocolate Bar Class

Chocolate Bar Class - Hands on class

$17
per adult
Chocolate Bar Class - Hands on class
Jacksonville Jaguars Football Game at EverBank Stadium

Jacksonville Jaguars Football Game at EverBank Stadium

$42
per adult
Jacksonville Jaguars Football Game at EverBank Stadium
See all activities in Jacksonville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.